N-(5-nitro-2-pyrrolidinylphenyl)trifluoroacetamide | 188997-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-(5-nitro-2-pyrrolidinylphenyl)trifluoroacetamide
• 英文别名: 2,2,2-Trifluoro-N-(5-nitro-2-(pyrrolidin-1-yl)phenyl)acetamide；2,2,2-trifluoro-N-(5-nitro-2-pyrrolidin-1-ylphenyl)acetamide
• CAS: 188997-85-5
• 化学式: C₁₂H₁₂F₃N₃O₃
• 分子量: 303.241
• InChiKey: QGXKMXWIRDSHGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氟-5-硝基苯胺 在 吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(5-nitro-2-pyrrolidinylphenyl)trifluoroacetamide
  参考文献：
  名称：

  N-(5-Nitro-2-pyrrolidinylphenyl)trifluoroacetamide

  摘要：

  The reaction of 2-fluoro-5-nitroaniline with pyrrolidine and triethylamine in DMF gives 2-pyrrolidinyl-5-nitroaniline, and subsequent treatment with trifluoroacetic acid and thionyl chloride in DMF results in the title compound, C12H12F3N3O3, the molecular structure of which, determined by X-ray crystallography, is described. In recent years, the interest in using organic crystals with a charge-transfer interaction via highly delocalized pi-electron states (e.g. nitroanilines with donor and acceptor substituents in para positions) has increased considerably, since many of them have shown non-linear optical properties [Chemla & Zyss (1986). In Nonlinear Optical Properties of Organic Molecules and Crystals, Vols. 1 and 2. Orlando: Academic Press]. N-(5-Nitro-2-pyrrolidinylphenyl)trifluoroacetamide (TPNB) is a donor-acceptor substituted benzene derivative and belongs to a family of compounds which produce high molecular non-linearity. TPNB shows a charge transfer (CT) between the para-disposed pyrrolidino donor and nitro acceptor groups.

  DOI：

  10.1107/s0108270196014679

文献信息

• <i>N</i>-(5-Nitro-2-pyrrolidinylphenyl)trifluoroacetamide
  作者：C. Yanes、M. Torres、M. López-Rodríguez、P. Núñez、I. Brito

  DOI：10.1107/s0108270196014679

  日期：1997.4.15

  The reaction of 2-fluoro-5-nitroaniline with pyrrolidine and triethylamine in DMF gives 2-pyrrolidinyl-5-nitroaniline, and subsequent treatment with trifluoroacetic acid and thionyl chloride in DMF results in the title compound, C12H12F3N3O3, the molecular structure of which, determined by X-ray crystallography, is described. In recent years, the interest in using organic crystals with a charge-transfer interaction via highly delocalized pi-electron states (e.g. nitroanilines with donor and acceptor substituents in para positions) has increased considerably, since many of them have shown non-linear optical properties [Chemla & Zyss (1986). In Nonlinear Optical Properties of Organic Molecules and Crystals, Vols. 1 and 2. Orlando: Academic Press]. N-(5-Nitro-2-pyrrolidinylphenyl)trifluoroacetamide (TPNB) is a donor-acceptor substituted benzene derivative and belongs to a family of compounds which produce high molecular non-linearity. TPNB shows a charge transfer (CT) between the para-disposed pyrrolidino donor and nitro acceptor groups.